6. Do Not Underestimate the Toll

You are going to feel an ocean of different things so prepare yourself and your loved ones

Problem Statement.

No one warns you how personal selling a business feels. On paper it is a commercial transaction. In your chest it can feel like pride, grief, relief, fear, excitement plus guilt taking turns at the wheel. Sometimes all before morning tea.

If you ignore that emotional load, it tends to leak out sideways. Snapping at staff. Rushing decisions. Agreeing to terms you later regret just because you cannot face one more tough conversation. Loved ones ride the waves with you whether they sign anything or not.

What An Owner Might Say.

“I thought the hard part would be due diligence. The hard part was holding myself together.”

“My partner was thrilled then furious then worried. I realised I had dragged them into my roller coaster without any kind of safety bar.”

“By the time we got to negotiation I was so tired I just wanted it over. Looking back, I wish I had taken better care of my head.”

Why It Happens.

For many owners the business is woven into identity. It is how you introduce yourself, where you spend most waking hours, the place you have poured stress and creativity for years. Selling can feel less like passing an asset and more like handing over a piece of self. There is no neutral way to experience that.

You are often the main shock absorber. Staff bring worries to you. Buyers push for concessions. Advisers warn you about risk. Family ask what life might look like next. Very few people ask how you are coping. You may even pride yourself on being the calm one so you swallow more than is healthy.

The process itself is uncertain. Timelines slip. Offers move. Banks hesitate. Deals fall over then restart. Your nervous system spends months half braced. That kind of chronic tension is exhausting, especially when you are still running the business day to day.

Money adds both pressure and expectation. This may be the biggest financial event of your life. Part of you wants to protect every dollar. Another part feels tempted to give some away, upgrade everything, fix every family issue in one heroic sweep. Without a plan, those impulses fight quietly in the background.

What To Do About It.

Accept from the start that you will not be at your calmest. Planning for that reality is not weakness. It is risk management for the human in the middle.

First, build a small personal support crew. Ideally this includes your partner or closest family member, one trusted friend who understands business, plus a professional such as a coach or counsellor who is not involved in the deal. Tell them plainly that this season may be bumpy and that you would value occasional reality checks.

Next, sketch your emotional non negotiables. For example

• I will not sign major documents when I am exhausted or angry.

• I will protect one or two evenings a week as genuinely work free.

• I will tell someone when I notice I am not sleeping or I am drinking more than usual.

Write these down. When the storm hits, written promises to yourself are easier to honour than vague intentions.

Talk with your loved ones early. Share the rough timeline, the level of uncertainty and how you expect to be affected. Ask what they need in order to feel informed yet not flooded. Some will want detail. Others will prefer headlines plus reassurance that you are seeking good advice. This conversation can feel awkward. It is far kinder than leaving them to guess from your mood.

Put simple routines around your physical health. Decent food, movement, sleep, a little daylight that is not through a windscreen. You have probably given this advice to staff for years. During an exit you finally need to listen to it yourself. Decisions around millions are rarely improved by running on fumes.

Set boundaries with advisers and buyers. Agree reasonable times for calls. Let them know you may need to sleep on big shifts. Clarify that family or key commitments are not negotiable. Professionals who respect you will work within those lines. If someone constantly drags you into late night panics, that is information about whether they belong in your next chapter.

How To Keep The Momentum.

Treat your emotional state as something to monitor, just like cash. Once a week, ask yourself three questions.

• How am I actually feeling about this process right now.

• Where am I starting to behave out of character.

• What small thing would make next week feel more manageable.

Share honest answers with someone in your support crew. Small course corrections now can prevent bigger wobbles later.

Watch for red flags. Constant arguments at home about the sale. Waking at three in the morning most nights. Snapping at staff you usually value. Fantasising about burning everything down. None of these mean the sale is wrong. They do mean you are carrying more than one person should. Take them as prompts to slow decisions, seek support or adjust timing if you can.

Plan for the “after” dip, not just the “before” stress. Many owners report a strange emptiness once the deal is done. Everyone congratulates you. You feel oddly flat. This is normal. You have gone from ultra busy to suddenly spacious. Before completion, sketch a light landing plan for the first three to six months. Rest, small projects, time with people you like, perhaps one purposeful commitment. Enough structure that you do not drift, yet not so much that you never exhale.

Be gentle with yourself if you feel regret or nostalgia. Selling a business is a big goodbye. Some days you will feel certain it was the right move. Some days you will miss the old chaos. Both can be true. What matters most is that the decision lined up with your values and life goals, not that every memory feels simple.

Golden Nugget.

“The deal is numbers on paper. The toll is the part no one sees unless you choose to share it.”

How RegenerationHQ can help.

RegenerationHQ exists to support owners through the whole experience of exit, not just the financial and legal steps. That means taking your emotional bandwidth seriously as a factor in how well the process goes.

Support can include structured conversations about how you are coping, help to pace the work, gentle challenge when you are about to make a big concession purely from exhaustion, plus space to think aloud about the impact on family and identity. RegenerationHQ also works alongside your accountant, lawyer and financial planner so that the human side sits beside the technical advice rather than underneath it.

Within the wider Exit Prep Programme, this focus on you helps shape timing, deal structure, handover plans and life after sale so that the toll feels bearable, not crushing. The aim is simple. When you look back, you remember a hard season handled with more care than chaos, for you and for the people who walked through it with you.

If you want a steady guide beside you while you get ready for one of the biggest decisions of your working life, RegenerationHQ is ready to help you walk that road with clarity and confidence.